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Compound Detail

CHEMBL395429

OXYTOCIN
💊 Approved Drug
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💊 Approved Drug
CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](N)CSSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O

Basic Information

ChEMBL ID CHEMBL395429
Name OXYTOCIN
Phase Approved
Structure Type BOTH
InChI Key XNOPRXBHLZRZKH-DSZYJQQASA-N
Therapeutic ✓ Yes

Known Names

Alpha-hypophamine Endopituitrina Intertocine s Orasthin Oxitocina Oxytocin Oxytocine Oxytocinum Pitocin Syntocinon Syntometrine TNX-1900 +2 more
9
Targets
69
Activities
4
Assay Types
11
PK Parameters
20
Publications
14
Known Names
20
Indications
1
Mechanisms

Molecular Properties

1007.2
MW (Da)

Drug Information

Molecule Type Protein
First Approval 1980
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -tocin

Extended Properties

Molecular Formula C43H66N12O12S2
MW 1007.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Oxytocin receptor agonist AGONIST Oxytocin receptor

Indications

Hemorrhage Uterine Inertia Alcoholism Child Development Disorders, Pervasive Dystocia Myoma Postpartum Hemorrhage Schizophrenia Tinnitus Aging Atrophic Vaginitis Atrophy Autistic Disorder Carcinoma, Intraductal, Noninfiltrating Chronic Pain Cocaine-Related Disorders Depressive Disorder Feeding and Eating Disorders Fragile X Syndrome Frontotemporal Dementia

ATC Classification

H01BB02
oxytocin
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 44 meas. best 11.0
Ki 22 meas. best 9.36
Kd 2 meas. best 8.17
IC50 1 meas. best 8.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxytocin receptor
CHEMBL2049
EC50 11.0 8.8283 0.0 18
Vasopressin V1a receptor
CHEMBL1889
EC50 9.74 8.2756 0.2 9
Vasopressin V1b receptor
CHEMBL1921
EC50 9.7 7.7267 0.2 6
Oxytocin receptor
CHEMBL2049
Ki 9.36 8.8536 0.4 11
Rattus norvegicus
CHEMBL376
EC50 9.3 9.26 0.5 2
Oxytocin receptor
CHEMBL3996
Ki 9.05 8.91 0.9 2
Myometrium
CHEMBL613647
EC50 8.77 8.77 1.7 1
Oxytocin receptor
CHEMBL3243907
EC50 8.7 8.7 2.0 1
Oxytocin receptor
CHEMBL2049
IC50 8.57 8.57 2.7 1
Oxytocin receptor
CHEMBL2049
Kd 8.17 8.17 6.7 2
Vasopressin V2 receptor
CHEMBL1790
EC50 8.14 7.1125 7.3 4
Vasopressin V1a receptor
CHEMBL1889
Ki 7.7 7.25 20.0 4
Vasopressin V2 receptor
CHEMBL3766
Ki 7.21 7.135 61.0 2
Vasopressin V2 receptor
CHEMBL1790
Ki 5.81 5.635 1544.0 2
Vasopressin V1b receptor
CHEMBL1921
Ki 5.75 5.75 1782.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 21.0 mL.min-1.kg-1 Rattus norvegicus
F 0.85 % Rattus norvegicus
T1/2 2.967 hr Rattus norvegicus
T1/2 11.6 hr Homo sapiens
T1/2 0.05 hr Rattus norvegicus
T1/2 0.03333 hr Mus musculus
T1/2 0.0485 hr Mus musculus
T1/2 0.1473 hr Mus musculus
T1/2 0.2538 hr Homo sapiens
T1/2 24.0 hr -
T1/2 0.1333 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxytocin receptor EC50 = 0.01 nM 11.0 Agonist activity at recombinant human OTR expressed in HEK293 cells assessed as ... 30896946
Oxytocin receptor EC50 = 0.04 nM 10.4 Agonist activity at human oxytocin receptor expressed in CHO cells assessed as i... 27297999
Oxytocin receptor EC50 = 0.04 nM 10.4 Agonist activity at human OTR expressed in CHO cells assessed as increase in cal... 29273395
Vasopressin V1a receptor EC50 = 0.18 nM 9.74 Agonist activity at human V1A receptor expressed in HEK293 cells assessed as int... 31229420
Vasopressin V1a receptor EC50 = 0.19 nM 9.72 Agonist activity at recombinant human V1a receptor expressed in HEK293 cells ass... 30896946
Vasopressin V1b receptor EC50 = 0.2 nM 9.7 Agonist activity at human V1B receptor expressed in HEK293 cells assessed as int... 31229420
Oxytocin receptor EC50 = 0.3 nM 9.52 Agonist activity at human mammary gland oxytocin receptor expressed in CHO cells... 29602673
Oxytocin receptor Ki = 0.44 nM 9.36 Displacement of [3H]8-arginine-vasopressin from human oxytocin receptor expresse... 27297999
Rattus norvegicus EC50 = 0.5 nM 9.3 Effective concentration in rat in the presence of 1 mM of Magnesium 10780900
Oxytocin receptor Ki = 0.58 nM 9.24 Displacement of [3H]OT from recombinant human OTR expressed in HEK293 cell membr... 30896946
Rattus norvegicus EC50 = 0.6 nM 9.22 Effective concentration in rat in the absence of Magnesium 10780900
Oxytocin receptor EC50 = 0.7 nM 9.15 Agonist activity at human OTR receptor expressed in HEK293FT cells assessed as s... 30199637
Oxytocin receptor Ki = 0.79 nM 9.1 Binding affinity to OTR (unknown origin) 25642985
Oxytocin receptor Ki = 0.8 nM 9.1 Displacement of [Tyrosyl-2,6-3H]-Oxytocin from recombinant human oxytocin recept... 26741855
Oxytocin receptor Ki = 0.8 nM 9.1 Binding affinity for human oxytocin receptor 12036367
Oxytocin receptor Ki = 0.79 nM 9.1 Displacement of [3H]OT from oxytocin receptor expressed in COS1 cells 21117646
Oxytocin receptor Ki = 0.79 nM 9.1 Competitive binding to oxytocin receptor (unknown origin) by radioligand binding... 25642985
Oxytocin receptor Ki = 0.89 nM 9.05 Binding affinity against oxytocin receptor in rat uterus 2167976
Oxytocin receptor Ki = 1.2 nM 8.92 Displacement of [3H]OT from human mammary gland oxytocin receptor expressed in H... 29602673
Oxytocin receptor EC50 = 1.28 nM 8.89 Agonist activity at recombinant human Gi/Go-coupled OTR expressed in CHOK1 cells... 31850759

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
10585209 10.1021/jm9900220 Rattus norvegicus 12
536993 10.1021/jm00198a011 ADMET 10
30896946 10.1021/acs.jmedchem.8b01691 ADMET 6
30199637 10.1021/acs.jmedchem.8b00697 Oxytocin receptor 6
10780900 10.1021/jm990090m Rattus norvegicus 6
23312470 10.1016/j.bmcl.2012.12.041 ADMET 6
30896946 10.1021/acs.jmedchem.8b01691 Mus musculus 6
25642985 10.1021/jm501395b Oxytocin receptor 6
6187921 10.1021/jm00358a018 Rattus norvegicus 5
6685771 10.1021/jm00366a028 Rattus norvegicus 5
30896946 10.1021/acs.jmedchem.8b01691 Oxytocin receptor 5
943546 10.1021/jm00225a007 Oxytocin receptor 4
30199637 10.1021/acs.jmedchem.8b00697 Vasopressin V2 receptor 4
30199637 10.1021/acs.jmedchem.8b00697 Vasopressin V1b receptor 4
7359537 10.1021/jm00176a020 Rattus norvegicus 4
29602673 10.1016/j.bmc.2018.03.019 Unchecked 4
833810 10.1021/jm00211a025 Rattus norvegicus 3
24874785 10.1021/jm500365s Unchecked 3
28438540 10.1016/j.bmcl.2017.04.030 Vasopressin V1a receptor 3

Data from ChEMBL 36 via Core Engine